Poly[3-(3,4-dihydroxyphenyl)Glyceric Acid] with Potential Therapeutic Effect

According to IR, 13C and 1H NMR, APT, 1D NOE, 2D heteronuclear 1H/13C HSQC and 2D DOSY experiments the main chemical constituent of high-molecular preparations from Symphytum asperum, S. caucasicum, S. officinale and Anchusa italica (Boraginaceae) was found to be caffeic acid-derived polyether, namely poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA) or poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene]. Most carboxylic groups of this polymer of A. italica are methylated.

Authors:

• V. Barbakadze
• L. Gogilashvili
• L. Amiranashvili
• M. Merlani
• K .Mulkijanyan

Keywords:

• Anchusa
• poly[3-(3
• 4-dihydroxyphenyl)glyceric acid]
• poly[oxy-1-carboxy-2-(3
• 4-dihydroxyphenyl)ethylene]
• Symphytum.

References:

[1] V. Barbakadze, E. Kemertelidze, I. Targamadze, K. Mulkijanyan, A. S.
Shashkov, and A. I.Usov, ”Poly(3-(3,4-dihydroxyphenyl)glyceric acid),
a new biologically active polymer from Symphytum asperum Lepech.
and S.caucasicum Bieb. (Boraginaceae)”, Molecules, vol. 10, no. 9, pp.
1135-1144, Sept. 2005.
[2] V. Barbakadze, A.J.J. van den Berg, C.J. Beukelman, J. Kemmink, and
H.C. Quarles van Ufford, “Poly(3-(3,4-dihydroxyphenyl)glyceric acid)
from Symphytum officinale roots and its biological activity”, Chem. Nat.
Compds., vol. 45, no. 1, pp. 6-10, January-February 2009.
[3] V. Barbakadze, L. Gogilashvili, L. Amiranashvili, M. Merlani, K.
Mulkijanyan, M. Churadze, A. Salgado, and B. Chankvetadze,
“Poly(3-(3,4-dihydroxyphenyl)glyceric acid) from Anchusa italica
roots”, Nat. Prod. Commun., vol. 5, no. 7, pp. 1091-1095, July 2010.
[4] V .Barbakadze, M. Merlani, L. Amiranashvili, L. Gogilashvili, and K.
Mulkijanyan. “Study of poly(oxy-1-carboxy-2-(3,4-
dihydroxyphenyl)ethylene) from Symphytum asperum, S.caucasicum,
S.officinale, Anchusa italica by circular dichroism”, Bull. Georg. Natl.
Acad. Sci., vol. 6, no. 1, pp. 143-146, January-April 2012.
[5] V. V. Barbakadze, E. P. Kemertelidze, K. G. Mulkijanyan, A. J. J.van
den Berg, C. J. Beukelman, E.van den Worm, H.C.Quarles van Ufford,
and A.I.Usov, “Antioxidant and anticomplementary activity of poly(3-
(3,4-dihydroxyphenyl)glyceric acid) from Symphytum asperum and S.
caucasicum”, Pharm. Chem. J., vol. 41, no 1, pp. 14-16, January 2007.
[6] C. M Barthomeuf, E. Debiton, V. V. Barbakadze, and E. P.
Kemertelidze. “Evaluation of the dietetic and therapeutic potential of a
high molecular weight hydroxicinnamate-derived polymer from
Symphytum asperum Lepech. Regarding its antioxidant,
antilipoperoxidant, antiinflammatory, and cytotoxic properties”, J.
Agric. Food Chem., vol. 49, no. 8, pp. 3942-3946, August 2001.
[7] V. Barbakadze, K. Mulkijanyan, L. Gogilashvili, L. Amiranashvili, M.
Merlani, Zh. Novikova, and M. Sulakvelidze, “Allantoin- and
pyrrolizidine alkaloids-free wound healing compositions from
Symphytum asperum”, Bull. Georg. Natl. Acad. Sci., vol. 3, no. 1, pp.
159-164, January-April 2009,
[8] K. Mulkijanyan,V. Barbakadze, Zh. Novikova, M. Sulakvelidze, L.
Gogilashvili, L. Amiranashvili, and M. Merlani, “Burn healing
compositions from Caucasian species of comfrey (Symphytum L.)”, Bull.
Georg. Natl. Acad. Sci.,. vol. 3, no. 3, pp. 114-117, September-
December 2009.
[9] V. Barbakadze, K. Mulkijanyan, M. Merlani, L. Gogilashvili, L.
Amiranashvili, and F. Vidal-Vanaclocha, “Effects of poly(3-(3,4-
dihydroxyphenyl)glyceric acid) on the inflammatory response of tumoractivated
hepatic sinusoidal endothelium”, Bull. Georg. Natl. Acad. Sci.,
vol. 2, no 3, pp. 108-112, July-September 2008.
[10] S. Shrotriya, G. Deep, K. Ramasamy, K. Raina, V. Barbakadze, M.
Merlani, L. Gogilashvili, L. Amiranashvili, K. Mulkijanyan,
K.Papadopoulos, C. Agarwal, and R. Agarwal. “Poly(3-(3, 4-
dihydroxyphenyl) glyceric) acid from comfrey exerts anti-cancer
efficacy against human prostate cancer via targeting androgen receptor,
cell cycle arrest and apoptosis”, Carcinogenesis, vol. 33, no. 8, pp.
1572-1580, August 2012.